GB839773A - Improvements in polyester resins from dicarboxylic acid anhydrides and monoepoxides - Google Patents
Improvements in polyester resins from dicarboxylic acid anhydrides and monoepoxidesInfo
- Publication number
- GB839773A GB839773A GB11143/57A GB1114357A GB839773A GB 839773 A GB839773 A GB 839773A GB 11143/57 A GB11143/57 A GB 11143/57A GB 1114357 A GB1114357 A GB 1114357A GB 839773 A GB839773 A GB 839773A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mols
- initiator
- anhydride
- acid
- dicarboxylic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title abstract 3
- 229920001225 polyester resin Polymers 0.000 title 1
- 239000004645 polyester resin Substances 0.000 title 1
- 239000003999 initiator Substances 0.000 abstract 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 5
- -1 carboxylhydroxyl Chemical group 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 4
- 229920000728 polyester Polymers 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 3
- 239000008096 xylene Substances 0.000 abstract 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 abstract 2
- 229960001553 phloroglucinol Drugs 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 abstract 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 abstract 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 abstract 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004386 Erythritol Substances 0.000 abstract 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N aconitic acid Chemical class OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 150000002118 epoxides Chemical group 0.000 abstract 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 abstract 1
- 235000019414 erythritol Nutrition 0.000 abstract 1
- 229940009714 erythritol Drugs 0.000 abstract 1
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical class O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 abstract 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical class O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 238000004382 potting Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000012970 tertiary amine catalyst Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
- C08G63/58—Cyclic ethers; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Thermoplastic polyesters having at least three linear polyester branch chains joined to a nucleus forming initiator (and in which the number of branch chains is equal to the functionality of said initiator and the length of each branch chain is theoretically equal to the total number of mols. of the monoepoxide (i) plus the number of mols. of the dicarboxylic anhydride, (iii) per mol. of the initiator (ii), divided by the functionality of the initiator) are prepared by reacting, without the formation of water and at temperatures at which carboxy-epoxy, phenolic hydroxyl-epoxy and alcoholic hydroxyl-anhydride reactions occur but below carboxylhydroxyl reaction temperatures, (i) a monoepoxide, (ii) an initiator having a functionality of at least three, and (iii) one or more dicarboxylic acid anhydrides; the mono-epoxide (i) being oxirane or an alkyl oxirane, or an ether or an ester containing only one three-membered epoxide substituent, and also being free of other groups capable of reacting with an acid anhydride; the initiator (ii) being a monomeric phenol or a monomeric or a polymeric ether, or an ester, or a polycarboxylic acid or a polyhydric alcohol, and also having at least three substituents of carboxylic, alcoholic hydroxyl, or phenolic hydroxyl radicals; wherein either the anhydride or the monoepoxide but not both, can be ethylenically unsaturated, the mol. ratio of (i) to (iii) being from 2:1 to 1:2 and the mol. ratio of (i) plus (iii) to (ii) being greater than 7:1. In general the process is carried out at temperatures of 120-150 DEG C. and a tertiary amine catalyst may be employed. The following compounds are specified: (i) ethylene-, propylene- and butene - 2 - oxides; phenyl-, isopropyl-, butyl- and allyl-glycidyl ethers; glycidyl-benzoate, -acrylate, -methacrylate, -crotonate and -acetate; (ii) pyromellitic, tricarballylic and aconitic acids; phloroglucinol and 1,2,4-trihydroxy-benzene; glycerol, erythritol, pentaerythritol, di- and poly-pentaerythritol, and sorbitol; castor oil; polyhydric alcohols which are the reaction product of 1 or 2 mols. of phthalic acid or anhydride with 2 or 3 mols. of pentaerythritol respectively; bis-phenol terminated bisphenol-epihalohydrin condensates which may or may not be partially esterified with a dicarboxylic acid or anhydride, and the bis-phenol-halohydrin condensate of Example (7) below; and a wide range of addition polymers, e.g. polyvinyl alcohol, the copolymers of vinyl toluene with hydroxypropyl-acrylate (see Example (12)) or acrylic acid, and of vinyl acetate with crotonic acid; (iii) succinic, adipic, maleic, glutaric, phthalic, sebacic, naphthalene dicarboxylic, endo-cis-bicyclo-(2,2,1)-5-heptene-2,3-dicarboxylic, and 1,4,5,6,7,7-hexachloro-bicyclo - (2,2,1) - 5 - heptene - 2,3 - dicarboxylic anhydrides. All three reagents may be reacted together or the initiator may be reacted first with one of the other reagents, the other being added later. In examples: (1)-(6), (8), (10) and (11) maleic and phthalic anhydrides and propylene oxide are reacted with glycerine, pentaerythritol, dipentaerythritol, pyromellitic acid, phloroglucinol or castor oil. (7) A polyhydroxy polyether is prepared from 5 mols. bisphenol A, 4 mols. epichlorhydrin, 2 mols. ethylene chlorhydrin and 6.9 mols. NaOH. The product which contains 6 hydroxyl groups is reacted with propylene oxide, and maleic and phthalic anhydrides. (9) as (7) but using butyl glycidyl ether in place of propylene oxide. In (1)-(8) and (11) the resultant polyesters, being unsaturated, are copolymerized with styrene which is inhibited with tert.-butyl catechol, in the presence of a paste of benzoyl peroxide and tricresyl phosphate. In (12) vinyl toluene, propylene oxide and acrylic acid are dissolved in xylene and methyl isobutyl ketone and are co-polymerized in the presence of benzoyl peroxide and a solution of benzyl trimethyl ammonium hydroxide in methanol. The resultant polymer, which is a co-polymer of vinyl toluene and hydroxy propyl acrylate, is reacted with propylene oxide and phthalic anhydride in (12)-(15); xylene, methyl isobutyl ketone and "Cellosolve" (Registered Trade Mark) acetate are used as solvents. In (W)-(Z) polyesters of earlier examples are mixed with butylated urea-formaldehyde resins, butyl alcohol, xylene, toluene and "Cellosolve" (Registered Trade Mark) acetate being used as solvents; the use of alkylated urea- or melamine-aldehyde resins in a similar way is discussed but not exemplified. Uses.-The resins may be used for potting, casting, moulding, laminating and coating (e.g. cables or wires) and in textile or adhesive applications.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US594716A US3089863A (en) | 1956-06-29 | 1956-06-29 | Process for preparation of a polyester resin of pentaerythritol, a dicarboxylic acid anhydride, and a monoepoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB839773A true GB839773A (en) | 1960-06-29 |
Family
ID=24380076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11143/57A Expired GB839773A (en) | 1956-06-29 | 1957-04-05 | Improvements in polyester resins from dicarboxylic acid anhydrides and monoepoxides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3089863A (en) |
| DE (3) | DE1246240B (en) |
| GB (1) | GB839773A (en) |
| NL (2) | NL120699C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337511A (en) * | 1963-08-24 | 1967-08-22 | Nippon Oil Co Ltd | Process of copolymerizing alkylene oxide and cyclic acid anhydride |
| US3412074A (en) * | 1964-08-07 | 1968-11-19 | Dow Chemical Co | 2-hydroxyalkyl acrylate copolymer-alpha, beta-unsaturated dicarboxylic acid partial esters |
| FR2283165A1 (en) * | 1974-09-02 | 1976-03-26 | Hoechst Ag | PROCESS FOR PREPARING POLYESTER RESINS HAVING A NARROW DISTRIBUTION OF MOLECULAR WEIGHTS |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275606A (en) * | 1961-06-01 | 1966-09-27 | Hooker Chemical Corp | Compositions containing adducts of hexahalocyclopentadiene |
| US3297596A (en) * | 1961-06-01 | 1967-01-10 | Hooker Chemical Corp | Polyurethanes containing adducts of hexahalocyclopentadiene |
| US3156740A (en) * | 1962-05-28 | 1964-11-10 | Rinshed Mason Company | Thermosetting mixture of a styrene-acrylic acid-epoxide-containing compound and an amine-aldehyde resin |
| US3251903A (en) * | 1962-11-09 | 1966-05-17 | Wyandotte Chemicals Corp | Cross-linked polyhalogenous polyester compositions prepared by reacting polyhalogenous epoxides with anhydrides |
| US3280077A (en) * | 1962-12-10 | 1966-10-18 | Leslie C Case | Resinous compositions comprising epoxy resins and polyester-ether copolymers having acidic end groups |
| US3372143A (en) * | 1963-05-31 | 1968-03-05 | Mitsubishi Rayon Co | Process for producing modified polyesters with epoxy ether compounds |
| US3609115A (en) * | 1963-09-30 | 1971-09-28 | North American Rockwell | Propellant binder |
| US3370043A (en) * | 1964-03-02 | 1968-02-20 | Jefferson Chem Co Inc | Method for preparing unsaturated polyesters |
| US3355434A (en) * | 1964-03-02 | 1967-11-28 | Jefferson Chem Co Inc | Method for preparing polyester resins |
| DE1544878A1 (en) * | 1964-08-08 | 1969-02-13 | Bayer Ag | Process for the gradual curing of unsaturated polyesters |
| US3459733A (en) * | 1964-10-15 | 1969-08-05 | Mobil Oil Corp | Monomeric polyesters of polyhydroxy compounds and process for preparing same |
| US3455886A (en) * | 1965-02-18 | 1969-07-15 | Columbian Carbon | Thermoplastic polyols containing polyester-ether blocks |
| US3376273A (en) * | 1965-09-20 | 1968-04-02 | Celanese Coatings Co | Polyester resin compositions and methods |
| US3376271A (en) * | 1965-09-20 | 1968-04-02 | Celanese Coatings Co | Polyester resins and method of making same |
| US3375301A (en) * | 1965-10-07 | 1968-03-26 | Leslie C. Case | Polymer compositions from vinyl monomers and unsaturated polyester-polyether copolymers |
| US4016142A (en) * | 1966-11-09 | 1977-04-05 | Millhaven Fibers, Ltd. | Process for the control of carboxyl end groups in fiber-forming polyesters |
| US3459715A (en) * | 1965-12-17 | 1969-08-05 | Monsanto Co | Alkyl glycidyl mixed esters and amine reaction products thereof |
| US3454530A (en) * | 1966-03-07 | 1969-07-08 | Leslie C Case | Novel polyols which are reaction products of a monoepoxide and a cyclic monoanhydride |
| US3483169A (en) * | 1967-08-21 | 1969-12-09 | Case Leslie C | Polyester-polyethers and process of preparing the same |
| US3493414A (en) * | 1967-10-12 | 1970-02-03 | Ashland Oil Inc | Epoxy/polyester compositions |
| US3627867A (en) * | 1968-09-05 | 1971-12-14 | Du Pont | Process of melt-spinning high-molecular-weight ethylene terephthalate polymer |
| US3912690A (en) * | 1970-11-05 | 1975-10-14 | Sherwin Williams Co | Method for producing a shellac substitute and product |
| JPS5328936B2 (en) * | 1971-12-03 | 1978-08-17 | ||
| JPS4920292A (en) * | 1972-06-16 | 1974-02-22 | ||
| US3931092A (en) * | 1974-04-29 | 1976-01-06 | Basf Wyandotte Corporation | Finely-divided polymeric solids having improved physical properties |
| US4314930A (en) * | 1980-05-07 | 1982-02-09 | Union Carbide Corporation | Composition containing a half ester of an organic polyol, an unsaturated monomer, an epoxide, and reinforcing fiber |
| US4313859A (en) * | 1980-05-07 | 1982-02-02 | Union Carbide Corporation | Composition containing a half ester of an organic polyol, an unsaturated monomer, an epoxide, and a basic compound |
| US4357430A (en) * | 1981-10-02 | 1982-11-02 | Union Carbide Corporation | Polymer/polyols, methods for making same and polyurethanes based thereon |
| US4403093A (en) * | 1982-09-28 | 1983-09-06 | Ppg Industries, Inc. | Polyesters |
| DE3307421A1 (en) * | 1983-03-03 | 1984-09-06 | Rhein-Chemie Rheinau Gmbh, 6800 Mannheim | PRODUCTION AND USE OF CROSS-LINKED, EPOXIDIZED FAT OILS |
| US4487853A (en) * | 1983-12-27 | 1984-12-11 | Basf Wyandotte Corporation | Low ethylene oxide/high primary hydroxyl content polyether-ester polyols and polyurethane foams based thereon |
| US4743655A (en) * | 1986-04-21 | 1988-05-10 | Nl Chemicals, Inc. | Narrow molecular weight polyester oligomers and method of preparation |
| US4789706A (en) * | 1986-04-21 | 1988-12-06 | Nl Chemicals, Inc. | Narrow molecular weight polyester oligomers and method of preparation |
| US5002976A (en) | 1989-02-23 | 1991-03-26 | Radcure Specialties, Inc. | Radiation curable acrylate polyesters |
| EP1335494A1 (en) * | 2001-12-19 | 2003-08-13 | Siemens Aktiengesellschaft | Sigma-delta converter with noise suppression |
| US7045564B2 (en) * | 2003-08-29 | 2006-05-16 | Albemarle Corporation | Flame retardants with high halogen content and low viscosity |
| CA2532162A1 (en) * | 2003-08-29 | 2005-03-17 | Albemarle Corporation | Flame retardants with high halogen content and low viscosity |
| CA3111001A1 (en) * | 2018-09-10 | 2020-03-19 | The University Of Akron | Star-shaped poly(propylene fumarate) copolymers for 3d printing applications |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1922459A (en) * | 1933-08-15 | Their production | ||
| US2056656A (en) * | 1927-10-17 | 1936-10-06 | Ellis Foster Co | Resin or balsam prepared with the aid of a reaction-modifier and process of making same |
| US1990615A (en) * | 1929-11-30 | 1935-02-12 | Ig Farbenindustrie Ag | Wax |
| US2197855A (en) * | 1932-04-07 | 1940-04-23 | Ellis Foster Co | Resin and method of making same |
| US2255313A (en) * | 1937-08-06 | 1941-09-09 | Ellis Foster Co | Ethylenic-alpha-beta synthetic resins and process of making same |
| US2652424A (en) * | 1951-05-14 | 1953-09-15 | Petrolite Corp | Acid fractional esters of oxypropylated hexanetriol-1, 2, 6 |
| US2720500A (en) * | 1952-10-17 | 1955-10-11 | Alkydol Lab Inc | Polyesters from polycarboxylic acids, polyhydric alcohols, and glycidyl ethers of monoh ydrocarbon substituted monohydric phenol |
| US2779783A (en) * | 1954-09-29 | 1957-01-29 | Firestone Tire & Rubber Co | Production of linear polyesters of alkylene dicarboxylic acids |
-
1956
- 1956-06-29 US US594716A patent/US3089863A/en not_active Expired - Lifetime
-
1957
- 1957-04-05 GB GB11143/57A patent/GB839773A/en not_active Expired
- 1957-04-26 DE DED25491A patent/DE1246240B/en active Pending
- 1957-04-26 DE DED37516A patent/DE1168632B/en active Pending
- 1957-04-26 DE DED36375A patent/DE1156555B/en active Pending
- 1957-04-26 NL NL216715A patent/NL120699C/en active
-
1964
- 1964-09-16 NL NL6410788A patent/NL6410788A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337511A (en) * | 1963-08-24 | 1967-08-22 | Nippon Oil Co Ltd | Process of copolymerizing alkylene oxide and cyclic acid anhydride |
| US3412074A (en) * | 1964-08-07 | 1968-11-19 | Dow Chemical Co | 2-hydroxyalkyl acrylate copolymer-alpha, beta-unsaturated dicarboxylic acid partial esters |
| FR2283165A1 (en) * | 1974-09-02 | 1976-03-26 | Hoechst Ag | PROCESS FOR PREPARING POLYESTER RESINS HAVING A NARROW DISTRIBUTION OF MOLECULAR WEIGHTS |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1168632B (en) | 1964-04-23 |
| NL216715A (en) | 1964-01-27 |
| DE1156555B (en) | 1963-10-31 |
| US3089863A (en) | 1963-05-14 |
| NL6410788A (en) | 1964-10-26 |
| NL120699C (en) | 1966-03-15 |
| DE1246240B (en) | 1967-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB839773A (en) | Improvements in polyester resins from dicarboxylic acid anhydrides and monoepoxides | |
| CA1059692A (en) | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids | |
| US3207718A (en) | Epoxy modified vinyl copolymers of alpha, beta-unsaturated dicarboxylic acid partialesters | |
| US3317465A (en) | Combination catalyst-inhibitor for betahydroxy carboxylic esters | |
| US3420914A (en) | Unsaturated polyester compositions and their preparation | |
| US3417045A (en) | Polymer composition | |
| US2826562A (en) | Hydroxy-substituted unsaturated esters prepared from polyepoxides and derivatives thereof | |
| US2934516A (en) | Carboxy-copolymer epoxide compositions and their preparation | |
| US2947712A (en) | Epoxide resin compositions | |
| US3247288A (en) | Carboxy copolymers prepared in 1, 2-epoxy compounds | |
| GB768748A (en) | Process for the preparation of fusible or liquid hydroxy-substituted allylic ethers and derivatives thereof | |
| GB1439719A (en) | Radiation-curable synthetic resins | |
| US4348506A (en) | Process for curing vinyl ester resins and composition useful therein | |
| GB1023374A (en) | Novel polymers, process for their preparation and products prepared therefrom | |
| US4357456A (en) | Low viscosity vinyl ester resins | |
| US3376272A (en) | Polyester resins | |
| GB1001670A (en) | Stoving finishes | |
| US3247145A (en) | Hydroxy copolymers prepared in carboxylic acids | |
| GB1197810A (en) | Thermosetting Ethylenically Unsaturated Ester Resin Compositions | |
| ES255317A1 (en) | Epoxide resin compositions | |
| GB1065721A (en) | Unsaturated polyesters and thermosetting products produced therefrom | |
| GB1115899A (en) | Novel polymers having pendent ester groups | |
| GB1023375A (en) | Wax emulsion compositions | |
| US4303579A (en) | Vinyl ester resins having improved color | |
| US4200705A (en) | Process for preparing blends of vinyl esters and reactive diluents |